Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2011 |
| Outros Autores: | , , , , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | por |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/36901 |
Resumo: | 2019-11-06 |
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Jordão, Alessandro K.Sathler, Plínio C.Ferreira, Vitor F.Campos, Vinícius R.Souza, Maria C. B. V. deCastro, Helena C.Lannes, AndressaLourenco, AndréRodrigues, Carlos R.Bello, Murilo L.Lourenço, Maria C. S.Carvalho, Guilherme S. L.Almeida, Maria C. B.Cunha, Anna C.2019-11-06T14:43:29Z2019-11-06T14:43:29Z2011JORDÃO, Alessandro K. et al. Synthesis, antitubercular activity, and SAR studyof N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides. Bioorganic and Medicinal Chemistry,0968-0896https://www.arca.fiocruz.br/handle/icict/3690110.1016/j.bmc.2011.07.035porElsevierSynthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazidesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article2019-11-06Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.Universidade Federal Fluminense. Departamento de Química Orgânica. Laboratório de Antibióticos, Bioquímica e Modelagem Molecular. Niterói, RJ, Brasil / Universidade Federal Fluminense. Hospital Universitário Antônio Pedro. Departamento de Patologia. Niterói, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.Universidade Federal Fluminense. Departamento de Química Orgânica. Laboratório de Antibióticos, Bioquímica e Modelagem Molecular. Niterói, RJ, Brasil / Universidade Federal Fluminense. Hospital Universitário Antônio Pedro. Departamento de Patologia. Niterói, RJ, Brasil.Universidade Federal Fluminense. Departamento de Química Orgânica. Laboratório de Antibióticos, Bioquímica e Modelagem Molecular. Niterói, RJ, Brasil / Universidade Federal Fluminense. Hospital Universitário Antônio Pedro. Departamento de Patologia. Niterói, RJ, Brasil.Universidade Federal Fluminense. Departamento de Química Orgânica. Laboratório de Antibióticos, Bioquímica e Modelagem Molecular. Niterói, RJ, Brasil / Universidade Federal Fluminense. Hospital Universitário Antônio Pedro. Departamento de Patologia. Niterói, RJ, Brasil.Universidade Federal do Rio de Janeiro. Laboratório de Modelagem Molecular & QSAR. Faculdade de Farmácia. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Laboratório de Modelagem Molecular & QSAR. Faculdade de Farmácia. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisa Evandro Chagas. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisa Evandro Chagas. Rio de Janeiro, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.Tuberculosis treatment remains a challenge that requires new antitubercular agents due to the emergence of multidrug-resistant Mycobacterium strains. This paper describes the synthesis, the antitubercular activity and the theoretical analysis of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides (8a–b, 8e–f, 8i–j and 8n–o) and new analogues (8c–d, 8g–h, 8l–m and 8p–q). These derivatives were synthesized in good yields and some of them showed a promising antitubercular profile. Interestingly the N-acylhydrazone (NAH) 8n was the most potent against the Mycobacterium tuberculosis H37Rv strain (MIC = 2.5 μg/mL) similar to or better than the current drugs on the market. The theoretical structure–activity relationship study suggested that the presence of the furyl ring and the electronegative group (NO2) as well as low lipophilicity and small volume group at R position are important structural features for the antitubercular profile of these molecules. NMR spectra, IR spectra and elemental analyses of these substances are reported.1,2,3-triazole derivativesDiazocompoundsCarbohydrazidesinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/36901/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51ORIGINALve_Jordão_Alessandro_etal_INI_2011.pdfve_Jordão_Alessandro_etal_INI_2011.pdfapplication/pdf658040https://www.arca.fiocruz.br/bitstream/icict/36901/2/ve_Jord%c3%a3o_Alessandro_etal_INI_2011.pdff38c29e24d358052a0b034c27b8a8c68MD52TEXTve_Jordão_Alessandro_etal_INI_2011.pdf.txtve_Jordão_Alessandro_etal_INI_2011.pdf.txtExtracted texttext/plain39238https://www.arca.fiocruz.br/bitstream/icict/36901/3/ve_Jord%c3%a3o_Alessandro_etal_INI_2011.pdf.txt5287f4b36bb0e733d334c0b4d2c93634MD53icict/369012021-03-24 16:32:24.967oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352021-03-24T19:32:24Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides |
| title |
Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides |
| spellingShingle |
Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides Jordão, Alessandro K. 1,2,3-triazole derivatives Diazocompounds Carbohydrazides |
| title_short |
Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides |
| title_full |
Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides |
| title_fullStr |
Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides |
| title_full_unstemmed |
Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides |
| title_sort |
Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides |
| author |
Jordão, Alessandro K. |
| author_facet |
Jordão, Alessandro K. Sathler, Plínio C. Ferreira, Vitor F. Campos, Vinícius R. Souza, Maria C. B. V. de Castro, Helena C. Lannes, Andressa Lourenco, André Rodrigues, Carlos R. Bello, Murilo L. Lourenço, Maria C. S. Carvalho, Guilherme S. L. Almeida, Maria C. B. Cunha, Anna C. |
| author_role |
author |
| author2 |
Sathler, Plínio C. Ferreira, Vitor F. Campos, Vinícius R. Souza, Maria C. B. V. de Castro, Helena C. Lannes, Andressa Lourenco, André Rodrigues, Carlos R. Bello, Murilo L. Lourenço, Maria C. S. Carvalho, Guilherme S. L. Almeida, Maria C. B. Cunha, Anna C. |
| author2_role |
author author author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Jordão, Alessandro K. Sathler, Plínio C. Ferreira, Vitor F. Campos, Vinícius R. Souza, Maria C. B. V. de Castro, Helena C. Lannes, Andressa Lourenco, André Rodrigues, Carlos R. Bello, Murilo L. Lourenço, Maria C. S. Carvalho, Guilherme S. L. Almeida, Maria C. B. Cunha, Anna C. |
| dc.subject.en.pt_BR.fl_str_mv |
1,2,3-triazole derivatives Diazocompounds Carbohydrazides |
| topic |
1,2,3-triazole derivatives Diazocompounds Carbohydrazides |
| description |
2019-11-06 |
| publishDate |
2011 |
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2011 |
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2019-11-06T14:43:29Z |
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2019-11-06T14:43:29Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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JORDÃO, Alessandro K. et al. Synthesis, antitubercular activity, and SAR studyof N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides. Bioorganic and Medicinal Chemistry, |
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https://www.arca.fiocruz.br/handle/icict/36901 |
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0968-0896 |
| dc.identifier.doi.pt_BR.fl_str_mv |
10.1016/j.bmc.2011.07.035 |
| identifier_str_mv |
JORDÃO, Alessandro K. et al. Synthesis, antitubercular activity, and SAR studyof N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides. Bioorganic and Medicinal Chemistry, 0968-0896 10.1016/j.bmc.2011.07.035 |
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https://www.arca.fiocruz.br/handle/icict/36901 |
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por |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Elsevier |
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Elsevier |
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